Dave "CAC" Kellogg and Ray "Growth" Rike tell the full story of how Intercom, a $400M ARR company that stalled at 4% growth, executed one of the most dramatic AI-first transformations in B2B SaaS. From writing off tens of millions in ARR to building a proprietary vertical AI model, this episode breaks down what it actually took to reinvent a mature SaaS business from the ground up.

Topics Covered

From 4% to 26% Growth: The Numbers Behind the Turnaround. Intercom hit rock bottom with five straight quarters of declining net new ARR before founder Eoghan McCabe returned and went all in on AI following the ChatGPT launch in November 2022. Ray and Dave walk through the growth trajectory and what made the timing of the reset both urgent and actionable.
The "Burn the Ships" Organizational Decision. Intercom rotated roughly 80% of its R&D team onto the new AI product, deliberately wrote off 50 to 60 million in ARR, and created small startup-like teams of 10 to 15 people with directly responsible individuals leading each workstream. Ray and Dave discuss why half-measures fail and how a stuck business actually has an advantage: very little to lose.
Board Dynamics and Why Committees Kill Bold Moves. Dave shares a candid take on how PE boards versus VC boards respond differently to dramatic pivots, and why the committee nature of multi-partner VC boards tends to drive toward measured, middle-ground responses that often produce no real outcome.
AI Economics: Gross Margins, Inference Costs, and Building Your Own Model. The shift from SaaS to AI-native changes the cost structure fundamentally. Ray puts current gross margin ranges in context (40 to 55% for pure AI-native, 55 to 70% for blended), explains why inference spend is actually rising despite lower per-token costs, and discusses why Intercom built its own vertical customer agent model for both performance and COGS optimization.
Outcome-Based Pricing and the 99-Cent Resolution. Customer support is one of the clearest use cases for outcome-based pricing because the natural unit is obvious: a resolved ticket. Ray and Dave break down how Intercom priced Fin at 99 cents per resolution, validated the model against an 81% internal resolution rate, and watched NRR climb from 112% to 146% as adoption scaled across 8,000 customers.
Never Waste a Good Crisis. Dave frames the broader lesson for SaaS CEOs: two paths exist now, dramatic AI reinvention or a Rule of 60/70 efficiency play. The Intercom story illustrates what the reinvention path actually demands. Ray adds that many SaaS companies sitting at 10% growth and 25% EBITDA are already in a slow-moving crisis and just haven't admitted it yet.

If you lead a B2B SaaS company navigating the shift to AI, this episode is the most concrete case study available on what full commitment actually looks like in practice. Ray and Dave go beyond the headlines to examine the organizational design, board dynamics, cost structure, pricing model, and retention metrics behind Intercom's transformation. Whether you are considering an AI-first pivot or trying to understand why incremental approaches tend to stall, this episode gives you the analytical framework and the real numbers to think it through.

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